1-Cyclohexenylboronic acid → HCID 58994563, compound

HRID 1508088Notes

Reaction equation

HRID 1508088 reaction equation
[C:1]1(B(O)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Br[C:11]1[CH:16]=[C:15]([CH2:17][S:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[CH:13][C:12]=1[NH2:27]>>[C:1]1([C:13]2[CH:14]=[C:15]([CH2:17][S:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)(=[O:20])=[O:19])[CH:16]=[CH:11][C:12]=2[NH2:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 58994392HCID 58994392, compound

Product 1

HCID 58994563HCID 58994563, compound

Procedure

The title compound was prepared according to the Suzuki coupling procedure of the Example 1, step (e) using cyclohex-1-enyl boronic acid (157 mg, 1.25 mmol) and 2-bromo-4-(morpholine-4-sulfonylmethyl)-phenylamine (as prepared in the previous step, 335 mg, 1.00 mmol) and purified on silica (20% EtOAc/hexanes) (276 mg, 82%). 1H-NMR (CDCl3; 400 MHz): δ 7.05 (dd, 1H, J=8.2, 1.9 Hz), 6.95 (d, 1H, J=1.9 Hz) 6.67 (d, 1H, J=8.2 Hz), 5.76 (br s, 1H), 4.12 (s, 2H), 3.90 (br s, 2H), 3.60-3.62 (m, 4H), 3.09-3.12 (m, 4H), 2.19-2.23 (m, 4H), 1.24-1.62 (m, 4H).

Workup

  1. customas prepared in the previous step, 335 mg, 1.00 mmol) and
  2. custompurified on silica (20% EtOAc/hexanes) (276 mg, 82%)

Sources & evidence

ORD record
ord-a87a0ca08c904c28853c011bbfb2420e
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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