Methyl 3-(bromomethyl)benzoate → HCID 58305367, compound

HRID 1805367Notes

Reaction equation

HRID 1805367 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.[Cl:13][C:14]1[CH:15]=[C:16]([C@@H:21]2[C@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[CH2:22]2)[CH:17]=[CH:18][C:19]=1[F:20]>>[Cl:13][C:14]1[CH:15]=[C:16]([C@@H:21]2[C@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:10][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=4)[C:3]([OH:2])=[O:12])[C:24]3=[O:32])[CH2:22]2)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

3

Reactant 2

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 67233507HCID 67233507, compound

Product 1

HCID 58305367HCID 58305367, compound

Procedure

The title compound was prepared in analogy to Example 1 starting from 3-bromomethyl-benzoic acid methyl ester (commercially available), (1R,2S) and (1S,2R)-2-(3-chloro-4-fluorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C24H17ClFNO3: 421, observed (M+H)+: 422.2 1H NMR (400 MHz, DMSO-d6) δppm 2.04-2.15 (m, 1 H) 2.40-2.49 (m, 1 H) 3.21 (t, 1 H) 5.09 (s, 2 H) 6.18 (d, 1 H) 6.75 (t, 1 H) 6.96 (d, 1 H) 7.06-7.14 (m, 1 H) 7.29-7.39 (m, 2 H) 7.46-7.53 (m, 1 H) 7.56-7.65 (m, 2 H) 7.82-7.93 (m, 2 H) 13.03 (s, 1 H).

Sources & evidence

ORD record
ord-713506ea6921418cad4026607a485249
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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