3-(Bromomethyl)-5-chloro-1-benzothiophene → HCID 57941416, compound

HRID 1438090Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.Br[CH2:17][C:18]1[C:19]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=2[S:21][CH:22]=1>CN(C)C=O>[Cl:27][C:25]1[CH:24]=[CH:23][C:20]2[S:21][CH:22]=[C:18]([CH2:17][N:3]3[C:4](=[O:15])[C:5]4[C@@H:6]5[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]5)[C:10]=4[N:2]3[CH3:1])[C:19]=2[CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 3-(bromomethyl)-5-chlorobenzo[b]thiophene (Maybridge plc, Tintagel, Cornwall, UK; 164 mg, 0.63 mmol) in dimethylformamide (5 mL) was heated at 100° C. for 2 days. The solvent was evaporated and ethyl acetate (50 mL) was added. The solution was washed with water (twice) and brine, dried (magnesium sulfate), filtered, evaporated and purified by chromatography, eluting with 1-3% methanol/dichloromethane to give (4S,7R)-2-(5-chloro-benzo[b]thiophen-3-ylmethyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (140 mg, 74%) as an off-white foam. APCI(+)-MS (M+H) 387.

Workup

customThe solvent was evaporated
additionethyl acetate (50 mL) was added
washThe solution was washed with water (twice) and brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
customevaporated
custompurified by chromatography
washeluting with 1-3% methanol/dichloromethane

Sources & evidence

ORD record: ord-9dcfa36269ff4938a10808902734f4e7
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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