Sodium Carbonate → HCID 86631032, compound

HRID 1806419Notes

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 Argon 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 Argon for 10 min
customCompound was purified by flash chromatography

Sources & evidence

ORD record: ord-f2023de3bd2644ac884363dc85f80e43
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354406B2

Reaction notes

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