Water → HCID 59851125, compound

HRID 2373405Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24](I)[CH:25]=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38].O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])[CH:25]=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of 2-(3,4-dimethoxy-phenylamino)-9-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-30) (300 mg, 0.614 mmol) in 4 mL DMF at 22° C. was added dichlorobis(triphenylphosphine)palladium (15 mg, 0.02 mmol), copper iodide (9 mg, 0.05 mmol), and triethylamine (0.34 mL, 2.45 mmol). The solution was degassed with argon, and stirred at 22° C. for 1 h. (Trimethylsilyl)acetylene (120 mg, 1.22 mmol) was added and the solution was stirred at 22° C. for 2 h. Water was added to the reaction mixture, and the resulting precipitate was filtered and purified by silica gel chromatography (ISCO, elution with 30-100% ethyl acetate in hexanes) to give I-33-a (180 mg, 64%): MS m/z═459 (M+H).

Workup

customThe solution was degassed with argon
additionwas added
filtrationthe resulting precipitate was filtered
custompurified by silica gel chromatography (ISCO, elution with 30-100% ethyl acetate in hexanes)
customto give I-33-a (180 mg, 64%)

Sources & evidence

ORD record: ord-5780c0d1a91742738480a2675244520f
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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