Cesium carbonate → HCID 86610749, compound

HRID 269981Notes

Reaction equation

HRID 269981 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH:33][CH2:34][CH2:35][NH:36][S:37]([C:40]2[C:41]3[CH:42]=[CH:43][N:44]=[CH:45][C:46]=3[CH:47]=[C:48](Br)[CH:49]=2)(=[O:39])=[O:38])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH:33][CH2:34][CH2:35][NH:36][S:37]([C:40]2[C:41]3[CH:42]=[CH:43][N:44]=[CH:45][C:46]=3[CH:47]=[C:48]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:49]=2)(=[O:39])=[O:38])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 86610750HCID 86610750, compound

Product 1

HCID 86610749HCID 86610749, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Add tetrakis(triphenylphosphine)palladium (0.816 g, 0.706 mmol) to a degassed mixture of phenylboronic acid (0.1.72 g, 14.1 mmol), cesium carbonate (9.20 g, 3.5928.2 mmol), and 7-bromo-isoquinoline-5-sulfonic acid (2-{[bis-(4-methoxy-phenyl)-methyl]-amino}-ethyl)-amide (3.93 g, 7.06 mmol) in toluene (75.0 mL) and water (100.0 mL). Warm to 100° C. for 2 hours, and cool to room temperature. Dilute with toluene (100 mL), separate layers, wash sequentially with water and brine, then dry with anhydrous MgSO4, filter and evaporate. Apply the residue to a cation exchange cartridge, wash the cartridge with methanol, and then elute with 2M methanolic ammonia. Evaporation affords the title compound (2.25 g, 58%). 1H NMR (DMSO): δ9.56 (s, 1H), 8.78(d, J=1.8 Hz, 1H), 8.70(d, J=6.2 Hz, 1H), 8.75(d, J=2.0 Hz, 1H), 8.45 (d, J=6.2 Hz, 1H), 7.91(d of t J1=1.3 Hz, J=7.0 Hz, 2H), 7.62(t of t, J1=1.7 Hz, J2=7.4 Hz, 2H), 7.53 (t of t, J1=1.3 Hz, J2=7.4 Hz, 1H), 7.04 (d of t, J1=1.7 Hz, J2=8.8 Hz, 4H), 6.72 (d of t, J1=1.7 Hz, J2=8.8 Hz, 4H), 4.44 (s, 1H), 3.68(s, 6H), 3.01 (t, J=6.1 Hz, 2H), 2.35 (t, J=5.9 Hz, 2H). LCMS: m/z 554 (M+H)+, 552(M−H).

Workup

  1. temperaturecool to room temperature
  2. customseparate layers
  3. washwash sequentially with water and brine
  4. dry with materialdry with anhydrous MgSO4
  5. filtrationfilter
  6. customevaporate
  7. washApply the residue to a cation exchange cartridge, wash the cartridge with methanol
  8. washelute with 2M methanolic ammonia
  9. customEvaporation

Sources & evidence

ORD record
ord-6d7c77cf4bfe484db6077c44b26f9861
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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