Cyanogen Bromide → HCID 68154608, compound

HRID 1183244Notes

Reaction equation

HRID 1183244 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]([N:10](C)[CH3:11])=[CH:8][CH:7]=1.N#CBr>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[CH:4]=[CH:5][C:6]1[CH:14]=[CH:13][C:9]([NH:10][CH3:11])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 10476Cyanogen BromideHCID 60141314HCID 60141314, compound

Product 1

HCID 68154608HCID 68154608, compoundYield 41%

Procedure

The procedure used to prepare 4 cc was repeated using 1 g (3.42 mmol) of 4y and 720 mg (6.84 mmol, 2 equiv) of cyanogen bromide to afford a product that was purified by chromatography (multiple times and each time using two developments) using 1:5 EtOAc-hexane to afford 390 mg (41%) of 4ee as a 9:1 E:Z-mixture of isomers that was a yellow oil. 1H NMR (DMSO-d6): δ 7.49 (d, 2H, J=8.4 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.24 (t, 1H, J=8.0 Hz), 6.99 (d, 1H, J=16.4 Hz), 6.82 (d, 1H, J=16.4 Hz), 6.55 (d, 2H, J=8.4 Hz), 6.01 (q, 1H, J=5.2 Hz), 2.70 (d, 3H, J=J5.2 Hz). 13C NMR (DMSO-d6): δ 150.45, 137.40, 134.69, 133.36, 128.86 (two C), 128.28, 127.97 (two C), 123.47, 116.09 (two C), 111.57 (two C), 29.50. HRMS (EI) Calcd for C15H13Cl2N, 277.0425. Found: 277.0425.

Workup

  1. customto prepare 4 cc
  2. customto afford a product that
  3. customwas purified by chromatography (multiple times

Sources & evidence

ORD record
ord-85866dd1033f4f83bd7f8d87e76befd8
Source dataset
uspto-grants-2014_03
Patent number
US08664276B2

Reaction notes

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