Bromotrimethylsilane → HCID 60111226, compound

HRID 1827002Notes

Reaction equation

HRID 1827002 reaction equation
CO[O:3][P:4]([O:9][CH2:10][CH:11]([OH:34])[CH2:12][O:13][C:14]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)/[C:18](=[CH:25]/[C:26]2[NH:27][C:28]([CH3:32])=[CH:29][C:30]=2[CH3:31])/[C:17]1=[O:33])=[O:15])([O:6]OC)=[O:5].C[Si](Br)(C)C>C(#N)C.ClCCl>[OH:34][CH:11]([CH2:10][O:9][P:4]([OH:5])([OH:6])=[O:3])[CH2:12][O:13][C:14]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)/[C:18](=[CH:25]/[C:26]2[NH:27][C:28]([CH3:32])=[CH:29][C:30]=2[CH3:31])/[C:17]1=[O:33])=[O:15]

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 87904723HCID 87904723, compound

Product 1

HCID 60111226HCID 60111226, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 3-(dimethoxy-phosphonooxy)-2-hydroxy-propyl ester (60 mg, 0.4 mmol) in 1.5 mL of acetonitrile and 1.5 mL of dichloromethane was added 52 μl (0.40 mmoL) of TMSBr dropwise. The reaction mixture was stirred for 6 h at room temperature and concentrated. The residue was quenched with 0.05 mL of water followed by 1.5 mL of EtOAc. The resultant mixture was centrifuged and the solvent was decanted. The precipitate was washed twice with ethyl acetate and dried to afford 120 mg (62%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-hydroxy-3-phosphonooxy-propyl ester as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 12.61 (s, 1H, NH-1′), 7.84 (dd, J=2.4, 8.0 Hz, 1H, H-4), 7.79 (dd, J=2.2, 6.8 Hz, 1H, H-7), 7.64 (s, 1H, H-vinyl), 7.16–7.21 (m, 2H, H-5, 6), 6.11 (s, br, 1H, H-4′), 4.40 (dd, J=4.0, 10.8 Hz, 1H), 4.32 (dd, J=5.8, 11.2 Hz, 1H), 4.00–4.05 (m, 1H) 3.90–3.93 (m, 2H), 2.37 (s, 3H, CH3), 2.33 (s, 3H, CH3). 31P NMR (162 MHz, d6-DMSO) δ 0.16.

Workup

  1. concentrationconcentrated
  2. customThe residue was quenched with 0.05 mL of water
  3. customthe solvent was decanted
  4. washThe precipitate was washed twice with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-0823b06744134adb9c2d42e0eec4dea6
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

Loading…