Bromocyclopentane → methyl 6-bromo-1-cyclopentyl-5-fluoro-1H-indole-3-carboxylate

HRID 1028019Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:15].Br[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][N:8]2[CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:4][C:3]=1[F:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 6-bromo-5-fluoro-1H-indole-3-carboxylate (9.0 g, 33 mmol), bromocyclopentane (5.3 mL, 49.6 mmol) and Cs2CO3 (21.5 g, 66 mmol) in DMF (40 mL) was stirred at 80° C. overnight. The mixture was then poured into ice water, filtered and washed with water. The solid was collected and dried to give methyl 6-bromo-1-cyclopentyl-5-fluoro-1H-indole-3-carboxylate (10.3 g, yield 91%), which was used in the next step without further purification.

Workup

filtrationfiltered
washwashed with water
customThe solid was collected
customdried

Sources & evidence

ORD record: ord-7a3b3a93986d4b2295efb5d3fb85a54d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735414B2

Reaction notes

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