Bromotrimethylsilane → HCID 178491166, compound

HRID 1525206Notes

Reaction equation

HRID 1525206 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:12]2[CH:17]=[CH:16][C:15]([P:18](=[O:25])([O:22]CC)[O:19]CC)=[CH:14][CH:13]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[N:3]=1.C[Si](Br)(C)C>ClCCl>[OH:1][C:2]1[C:7]([C:8]([NH:10][CH:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:12]2[CH:13]=[CH:14][C:15]([P:18](=[O:19])([OH:22])[OH:25])=[CH:16][CH:17]=2)=[O:9])=[CH:6][N:5]=[C:4]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[N:3]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476966HCID 178476966, compound

Product 1

HCID 178491166HCID 178491166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl phosphate (1-1-1, 260 mg, 0.47 mmol) in dichloromethane (10 ml) was added TMSBr (2.18 g, 14.2 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 3 days. The mixture was concentrated under vacuum and methanol (20 ml) was added. The mixture was stirred for 15 mins at room temperature and concentrated. The residue was purified on prep-HPLC to provide the product, 1-1-2. (100 mg, 43%). 1H NMR (DMSO-d6, 300 MHz,): δ 8.81 (d, 1H, J=6 Hz), 8.40 (m, 1H), 8.10 (m, 1H), 7.60 (m, 4H), 7.35 (m, 2H), 7.25 (m, 2H), 6.95 (m, 2H), 6.23 (d, 1H, J=6 Hz), 3.71 (s, 3H). (M−H)−=491.1.

Workup

  1. concentrationThe mixture was concentrated under vacuum and methanol (20 ml)
  2. additionwas added
  3. stirringThe mixture was stirred for 15 mins at room temperature
  4. concentrationconcentrated
  5. customThe residue was purified on prep-HPLC
  6. customto provide the product, 1-1-2

Sources & evidence

ORD record
ord-4c8e2a2e36f24017a59461210e20e228
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…