Cyanogen Bromide → FIDAS-5

HRID 1183243Notes

Reaction equation

HRID 1183243 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F: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]([F: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 60141313HCID 60141313, compound

Product 1

HCID 57521314FIDAS-5

Procedure

The procedure used to prepare 4 cc was repeated using 1 g (3.63 mmol) of 4x and 764 mg (7.26 mmol, 2 equiv) of cyanogen bromide to afford a product that was purified by chromatography using 1:5 EtOAc-hexane to afford 400 mg (42%) of 4dd as a yellow solid: mp 43-45° C. 1H NMR (DMSO-d6): δ 7.37-7.31 (m, 3H), 7.27-7.21 (m, 2H), 7.18 (d, 1H, J=16.4 Hz), 6.88 (d, 1H, J=16.4 Hz), 6.56 (d, 2H, J=8.8 Hz), 6.04 (q, 1H, J=5.2 Hz), 2.71 (d, 3H, J=5.2 Hz). 13C NMR (DMSO-d6): δ 160.75 (d, J=248.0 Hz), 150.98, 137.24 (d, J=12.2 Hz), 133.30 (d, J=6.1 Hz), 128.49 (two C), 128.33 (d, J=9.9 Hz), 126.28 (d, J=3.1 Hz), 124.73 (d, J=14.5 Hz), 124.40, 115.54 (d, J=22.9 Hz), 113.12 (d, J=2.2 Hz), 112.11 (two C), 29.94. MS: m/z (%) 261 (100), 227 (15), 213 (25). Anal. Calcd for C15H13Cl FN: C, 68.84; H, 5.01. Found: C, 68.67; H, 5.05.

Workup

  1. customto prepare 4 cc
  2. customto afford a product that
  3. customwas purified by chromatography
  4. customto afford 400 mg (42%) of 4dd as a yellow solid

Sources & evidence

ORD record
ord-8a5393c719b44ed9bad292d42d256d2f
Source dataset
uspto-grants-2014_03
Patent number
US08664276B2

Reaction notes

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