Sodium Carbonate → HCID 86631032, compound

HRID 562237Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][C:4]=1[CH:5]=[O:6].Br[C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([C:30]([NH2:32])=[O:31])[CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:33]1[CH2:38][CH2:37][N:36]([S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])[CH2:35][CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH2:42]([S:39]([N:36]1[CH2:35][CH2:34][CH:33]([C:24]2[C:23]3[C:27](=[C:28]([C:30]([NH2:32])=[O:31])[CH:29]=[C:21]([C:8]4[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:5]=[O:6])[CH:7]=4)[CH:22]=3)[NH:26][CH:25]=2)[CH2:38][CH2:37]1)(=[O:41])=[O:40])[CH3:43]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (610 mg, 2.33 mmol) in dioxane (19 mL) and H2O (6.3 mL), was added 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (963 mg, 2.33 mmol), and sodium carbonate (1.48 g, 13.9 mmol). After flushing with Agron for 10 min, tetrakis(triphenylphosphine)palladium(0) (134 mg, 0.166 mmol) was added. The reaction was heated in the microwave 120° C. for 120 min. Compound was purified by flash chromatography using DCM and MeOH to give 632 mg of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-formyl-4-(methyloxy)phenyl]-1H-indole-7-carboxamide (58%).

Workup

customAfter flushing with Agron for 10 min
customCompound was purified by flash chromatography

Sources & evidence

ORD record: ord-b6d5342703da4414a4ae1ca541afe642
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063071B2

Reaction notes

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