Sodium Carbonate → HCID 178420009, compound

HRID 1023847Notes

Reaction equation

HRID 1023847 reaction equation
C([O-])([O-])=O.[Na+].[Na+].I[C:8]1[N:9]=[CH:10][NH:11][CH:12]=1.C(OC([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1B(O)O)=O)(C)(C)C>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.CN(C=O)C>[NH:11]1[CH:12]=[C:8]([C:21]2[NH:20][C:28]3[C:23]([CH:22]=2)=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:9]=[CH:10]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 178506559HCID 178506559, compound

Product 1

HCID 178420009HCID 178420009, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of DMF (3 mL) and 2M Na2CO3 (0.75 mL) was purged with nitrogen for 10 minutes. 4-iodo-1H-imidazole (145.5 mg, 0.75 mmol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (235.0 mg, 0.9 mmol) and Pd(PPh3)4 (86.7 mg, 75.0 μmol) were added followed by purging with nitrogen for an additional 2 minutes. The solution was heated at 85° C. over night. The solution was poured into water (20 mL) and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with water (2×10 mL), brine and dried. The solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel using 10% MeOH/DCM as the eluent. The BOC protecting group was lost during the reaction sequence. Yield=37%. 1H NMR: 6.66 (s, 1H), 7.07-7.15 (m, 2H), 7.32 (s, 1H), 7.33 (d, 1H, J=7.8 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.63 (s, 1H), 9.47 (s, 1H).

Workup

  1. customwas purged with nitrogen for 10 minutes
  2. customby purging with nitrogen for an additional 2 minutes
  3. additionThe solution was poured into water (20 mL)
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water (2×10 mL), brine
  6. customdried
  7. customThe solvent was removed under reduced pressure
  8. customthe crude residue was purified by column chromatography on silica gel using 10% MeOH/DCM as the eluent

Sources & evidence

ORD record
ord-10b9d8b4eed747f9a6212b6f56433dce
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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