Bromotrimethylsilane → HCID 69595139, compound

HRID 1827013Notes

Reaction equation

HRID 1827013 reaction equation
CO[O:3][P:4]([O:9][CH2:10][CH2:11][O:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)/[C:17](=[CH:24]/[C:25]2[NH:26][C:27]([CH3:31])=[CH:28][C:29]=2[CH3:30])/[C:16]1=[O:32])=[O:14])([O:6]OC)=[O:5].Br[Si](C)(C)C>C(#N)C>[P:4]([O:9][CH2:10][CH2:11][O:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)/[C:17](=[CH:24]/[C:25]2[NH:26][C:27]([CH3:31])=[CH:28][C:29]=2[CH3:30])/[C:16]1=[O:32])=[O:14])([OH:6])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 87904687HCID 87904687, compound

Product 1

HCID 69595139HCID 69595139, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the suspension of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-(dimethoxy-phosphonooxy)-ethyl ester (180 mg, 0.4 mmol) in 12 mL of acetonitrile was added bromotrimethylsilane (120 mL, 0.91 mmol) and N,O-bis-(trimethylsily)acetamide (225 mL, 0.91 mmol) sequentially. The reaction mixture was then stirred at room temperature for 42 h and concentrated. The residue was then washed with ethyl acetate, water, and 0.1 N HClaq and dried in a vacuum oven to yield 75 mg (37%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-ethyl ester as a red solid. 1H NMR (400 MHz, CDCl3) δ 12.40 (s, br, 1H, NH-1′), 7.84–7.86 (m, 1H, H-4), 7.76–7.79 (m, 1H, H-7), 7.63 (s, 1H, H-vinyl), 7.19–7.22 (m, 2H, H-5, 6), 6.11 (d, J=1.95 Hz, 1H, H-4′), 4.52–4.56 (m, 2H, NCOOCH2CH2OPO(OCH3)2-1), 4.15–4.19 (m, 2H, NCOOCH2CH2OPO(OCH3)2-1), 2.37 (s, 3H, CH3), and 2.33 (s, 3H, CH3).

Workup

  1. concentrationconcentrated
  2. washThe residue was then washed with ethyl acetate, water, and 0.1 N HClaq
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7b374bf984dd44caaaad878ae4da5947
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

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