Methyl 4-(bromomethyl)benzoate → (1R,2S)-N-(cyclopropylsulfonyl)-4-((2-(4-fluorophenyl)-2'-oxospiro [cyclopropane-1,3'-indoline]-1'-yl)methyl)benzamide

HRID 1805380Notes

Reaction equation

HRID 1805380 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[CH:13]1([S:16]([NH2:19])(=[O:18])=[O:17])[CH2:15][CH2:14]1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]2[C@:29]3([C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:38])[CH2:28]2)=[CH:23][CH:22]=1>>[CH:13]1([S:16]([NH:19][C:3](=[O:12])[C:4]2[CH:5]=[CH:6][C:7]([CH2:10][N:31]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C@:29]4([CH2:28][C@H:27]4[C:24]4[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=4)[C:30]3=[O:38])=[CH:8][CH:9]=2)(=[O:18])=[O:17])[CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 15765418CyclopropanesulfonamideHCID 67233318HCID 67233318, compound

Product 1

HCID 67232890(1R,2S)-N-(cyclopropylsulfonyl)-4-((2-(4-fluorophenyl)-2'-oxospiro [cyclopropane-1,3'-indoline]-1'-yl)methyl)benzamide

Procedure

The title compound was prepared in analogy to Example 60 starting from 4-bromomethyl-benzoic acid methyl ester, cyclopropanesulfonamide (commercially available), (1R,2S) and (1S,2R)-2-(4-fluorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C27H23FN2O4S: 490, observed (M+H)+: 491.2 1H NMR (400 MHz, DMSO-d6) δppm 0.70-0.81 (m, 2 H) 0.84-0.91 (m, 2 H) 2.06-2.17 (m, 1 H) 2.31-2.40 (m, 1 H) 2.91-3.02 (m, 1 H) 3.14-3.24 (m, 2 H) 5.04 (s, 2 H) 6.09 (d, 1 H) 6.68 (t, 1 H) 6.89 (d, 1 H) 7.05 (t, 2 H) 7.11-7.19 (m, 3 H) 7.89 (d, 2 H).

Sources & evidence

ORD record
ord-5cfa8d59279345eda39bb40840f9813b
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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