Methyl 4-(bromomethyl)benzoate → HCID 53247649, compound
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.[O:13]=[C:14]1[C@:22]2([CH2:24][C@@H:23]2[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15]1>>[C:29]([C:28]1[CH:27]=[CH:26][C:25]([C@H:23]2[C@@:22]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:12])=[CH:5][CH:6]=4)[C:14]3=[O:13])[CH2:24]2)=[CH:32][CH:31]=1)#[N:30]Participants
3
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)-4-(2′-oxospiro[cyclopropane-1,3′-indoline]-2-yl)benzonitrile prepared as in Scheme 1. LC/MS m/e calcd. for C25H18ClN2O3: 394, observed (M+H)+: 395.2 1H NMR (400 MHz, DMSO-d6) δppm 2.11-2.20 (m, 1 H) 2.43-2.50 (m, 1 H) 5.10 (s, 2 H) 6.16 (d, 1 H) 6.70 (t, 1 H) 6.92 (d, 1 H) 7.08 (t, 1 H) 7.43 (d, 2 H) 7.55 (d, 2 H) 7.80 (d, 2 H) 7.93 (d, 2 H).
Sources & evidence
- ORD record
- ord-9fec002a17814f6e9586b04b7f9aac20
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354443B2
Reaction notes
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