Methanol → HCID 68752610, compound

HRID 624247Notes

Reaction equation

HRID 624247 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]3[CH2:26][C:25]4[CH:24]=[CH:23][N:22]=[CH:21][C:20]=4[CH2:19]3)=[O:17])=[CH:11][CH:10]=2)O1.FC(F)(F)S(O[C:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36][CH:35]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].CO>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[CH2:26]1[C:25]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[CH2:19][N:18]1[C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([C:34]2[CH2:39][CH2:38][CH:37]([NH:40][C:41](=[O:42])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[CH2:36][CH:35]=2)=[CH:14][CH:13]=1)=[O:17]

Participants

8

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 598321994-[(tert-Butoxycarbonyl)amino]cyclohex-1-en-1-yl trifluoromethanesulfonateHCID 68753732HCID 68753732, compound

Product 1

HCID 68752610HCID 68752610, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxamide (1.692 g, 4.63 mmol), 4-(tert-butoxycarbonylamino)cyclohex-1-enyl trifluoromethanesulfonate (1.6 g, 4.63 mmol) and cesium carbonate (3.77 g, 11.58 mmol) were suspended in terahydrofuran (30 ml), methanol (5.00 ml) and water (15.00 ml). Nitrogen was bubbled throught the solution for 10 min when PdCl2(dppf)-dichloromethane adduct (0.189 g, 0.232 mmol) was added and the mixture was heated to 80° C. for 7 h. After dilution with ethyl acetate and brine, the separated aqueous layer was extracted several times with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography provided the title compound.

Workup

  1. customNitrogen was bubbled
  2. customfor 10 min
  3. additionwas added
  4. extractionAfter dilution with ethyl acetate and brine, the separated aqueous layer was extracted several times with ethyl acetate
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c62184a3dad34bc1b9102857b07f4c4b
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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