Ethyl 2,2-difluoropropanoate → HCID 59339681, compound

HRID 13215Notes

Reaction equation

HRID 13215 reaction equation
[F:1][C:2]([F:9])([CH3:8])[C:3](OCC)=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([O:26][C@H:27]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=4)[C@@H:28]([NH2:30])[CH3:29])=[CH:23][CH:24]=3)[CH:19]=[N:18]2)=[CH:13][CH:12]=1>C(#N)C>[F:1][C:2]([F:9])([CH3:8])[C:3]([NH:30][C@@H:28]([CH3:29])[C@H:27]([O:26][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[N:17]([C:14]1[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=1)[N:18]=[CH:19]2)[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=1)=[O:4]

Participants

4

Reactant 2

HCID 2761188Ethyl 2,2-difluoropropanoateHCID 59339733(1R,2S)-1-(1-(4-fluorophenyl)indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine

Product 1

HCID 59339681HCID 59339681, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2,2-difluoropropanoate (400 μl) and (1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine (6a, 135 mg, 0.34 mmol) was heated to 150° C. for 30 min. Then it was diluted with acetonitrile and purified by semiprep HPLC followed by flash chromatography on silica gel (n-heptane/ethyl acetate, 4:1) Yield 60 mg (36%).

Workup

  1. custompurified by semiprep HPLC

Sources & evidence

ORD record
ord-e4fda28d383d4f0894603e5dff2c1df9
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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