3-Bromopyridine → HCID 58306935, compound

HRID 1909884Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]=4[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[CH:15]3)=[CH:11][CH:10]=2)O1.[F-].[Cs+].Br[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]=4[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[CH:15]3)=[CH:11][CH:10]=2)[CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To methyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]-1H-indole-7-carboxylate (0.15 g), 1,1′-bis(diphenylphosphino)ferrocene palladium (14 mg), cesium fluoride (0.17 g), and 3-bromopyridine (79 mg) was added dioxane (4.5 mL), followed by stirring at 100° C. for 21 hours under an argon atmosphere. The reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/1) to obtain methyl 1-(4-pyridin-3-yl benzyl)-1H-indole-7-carboxylate (0.13 g).

Workup

customThe reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=2/1-1/1)

Sources & evidence

ORD record: ord-21e0bca6e10048599626293cfb17f9de
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598355B2

Reaction notes

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