Methyl 4-(bromomethyl)benzoate → HCID 58305385, compound

HRID 1805364Notes

Reaction equation

HRID 1805364 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:19]2[C@:21]3([C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][C:22]3=[O:30])[CH2:20]2)[CH:14]=1>>[O:30]=[C:22]1[C@:21]2([CH2:20][C@@H:19]2[C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]1[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:12])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 67234032HCID 67234032, compound

Product 1

HCID 58305385HCID 58305385, compound

Procedure

The title compound was prepared in analogy to Example 1 starting from 4-bromomethyl-benzoic acid methyl ester (commercially available), (1R,2S) and (1S,2R)-2-(pyridin-3-yl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C23H18ClN2O3: 370, observed (M+H)+: 371.2 1H NMR (400 MHz, DMSO-d6) δppm 2.14-2.23 (m, 1 H) 3.30 (t, 1 H) 5.10 (s, 2 H) 6.14 (d, 1 H) 6.70 (t, 1 H) 6.93 (d, 1 H) 7.10 (t, 1 H) 7.45 (d, 2 H) 7.57-7.65 (m, 1 H) 7.93 (d, 2 H) 8.06 (d, 1 H) 8.61 (d, 1H) 8.71 (s, 1 H).

Sources & evidence

ORD record
ord-c9ad39f56d6f434cbd7ed5420c54c02a
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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