3-Methylsulfonylaminophenylboronic acid → HCID 68937148, compound

HRID 2218697Notes

Reaction equation

HRID 2218697 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:23]=[CH:24][CH:25]=[CH:26][C:4]1=2.[CH3:27][S:28]([NH:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:30])=[O:29]>>[N:17]1([CH2:16][CH2:15][O:14][C:12]2[CH:11]=[CH:10][C:9]3[C:3](=[CH:2][C:34]4[CH:33]=[C:32]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])[CH:37]=[CH:36][CH:35]=4)[C:4]4[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=4[CH2:6][CH2:7][C:8]=3[CH:13]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 68938873HCID 68938873, compound

Product 1

HCID 68937148HCID 68937148, compound

Procedure

Following procedures essentially as described in Example 219, below, and using 4-[2-(5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yloxy)-ethyl]-morpholine (220 mg, 0.53 mmol) and 3-methanesulfonamidophenylboronic acid (125 mg, 0.58 mmol). Purification on silica gel eluting with EtOAc then EtOAc/1% MeOH/NH3, gave 57 mg of pure E-isomer. MS (ES)505 (M+1), 503(M−1). HPLC shows 92% purity at t=1.79 min.

Workup

  1. customPurification on silica gel eluting with EtOAc
  2. customEtOAc/1% MeOH/NH3, gave 57 mg of pure E-isomer
  3. customat t=1.79 min.

Sources & evidence

ORD record
ord-f2e435e853d647c0b50b685d618d57a2
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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