Methanol → HCID 69318044, compound

HRID 2113596Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([NH:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:28]#[N:29])[CH:5]=[CH:6][CH:7]=1.[CH2:30]([Sn](CCCC)(CCCC)C#CC)[CH2:31][CH2:32]C.CO>C1(C)C=CC=CC=1.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][NH:19][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][N:15]=2)[N:12]=[CH:11][C:10]([C:28]#[N:29])=[C:9]3[NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:30]#[C:31][CH3:32])[CH:3]=2)[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(3-iodophenylamino)-6-(2-morpholinoethylamino)-1,7-naphthyridine-3-carbonitrile (105.6 mg, 0.21 mmol, 1 eq) and tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.02 mmol, 0.1 eq) was taken up in toluene (2.5 mL) in microwave tube. Tributyl(prop-1-ynyl)stannane (193 uL, 0.63 mmol, 3 eq) was added to the mixture. The tube was sealed and heated 150° C. for 1 hr. Work-up followed by chromatography (1-3% Methyl alcohol in dichloromethane), yielded 35.6 mg product (41% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 2.04 (s, 3 H) 2.40-2.46 (m, 4 H) 2.55 (t, J=6.69 Hz, 2 H) 3.30-3.40 (m, 2 H) 3.55-3.60 (m, 4 H) 6.64 (t, J=5.68 Hz, 1 H) 7.01 (s, 1 H) 7.23 (s, 1 H) 7.25 (s, 2 H) 7.34-7.40 (m, 1 H) 8.28 (s, 1 H) 8.84 (s, 1 H) 9.61 (s, 1 H).

Workup

customThe tube was sealed

Sources & evidence

ORD record: ord-103ddeecb6b9481cb23ea0ecb03a3bce
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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