Triethylamine → HCID 178519313, compound

HRID 1615216Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.CCN(CC)CC.[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)#[CH:21]>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>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:20]#[C:21][C:2]2[C:10]3[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=3)[NH:4][N:3]=2)[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-iodo-1H-indazole-6-carbaldehyde (136 mg, 0.5 mmol), Pd(PPh3)2Cl2 (14 mg, 0.02 mmol) and CuI (7.6 mg, 0.04 mmol) in DMF (3 mL) was added Et3N (5 mL), followed by 3-ethynylpyridine (77 mg, 0.75 mmol). The resulting mixture was heated at 100° C. (oil temp.) for 45 min. After removal of Et3N, the residue was loaded directly onto a silical gel column. Flash chromatography (eluent: hex to ethyl acetate), followed by trituration with water and suction filtration gave the title compound (112 mg, 91%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 14.16 (s, 1H), 10.16 (s, 1H), 8.90 (s, 1H), 6.64 (d, J=4.0 Hz, 1H), 8.26 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 8.07 (d, J=8.4 Hz, 1H), 7.74 (d, J=8.4 Hz, 1H), 7.52 (dd, J=8.0 Hz, J=5.2 Hz, 1H); MS ESI 248.0 [M+H]+, calcd for [C15H9N3O+H]+ 248.1.

Workup

customAfter removal of Et3N
filtrationFlash chromatography (eluent: hex to ethyl acetate), followed by trituration with water and suction filtration

Sources & evidence

ORD record: ord-5cf102f410074684a6ee5073fa1f413a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

Loading…