3,3-Dimethyl-1-butyne → HCID 86629593, compound

HRID 911213Notes

Reaction equation

HRID 911213 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[CH3:27][C:28]([CH3:32])([CH3:31])[C:29]#[CH:30]>>[CH3:27][C:28]([CH3:32])([CH3:31])[C:29]#[C:30][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[CH2:7][CH2:6][C:5]=2[CH:17]=[CH:18][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 57656438HCID 57656438, compound

Product 1

HCID 86629593HCID 86629593, compoundYield 85.4%

Procedure

Use a method similar to the General Procedure 3 to couple 7-fluoro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1 g, 2.4 mmol) with 3,3-dimethyl-1-butyne (0.599 mL, 4.9 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1) to give 6-(3,3-dimethyl-but-1-ynyl)-7-fluoro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (700 mg, 84%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-1b227152a6dc44c3b78bf96081da8014
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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