Boron Trichloride → HCID 178463348, compound

HRID 44116Notes

Reaction equation

C([O:8][C:9]1[C:14]([N:15]([CH2:20][CH3:21])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:24]([C:25]([NH:27][CH3:28])=[O:26])=[C:11]2[CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:20]([N:15]([C:14]1[C:9]([OH:8])=[CH:10][C:11]2[N:12]([N:22]=[C:23]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[C:24]=2[C:25]([NH:27][CH3:28])=[O:26])[CH:13]=1)[S:16]([CH3:19])(=[O:17])=[O:18])[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

5-(Benzyloxy)-6-(N-ethylmethylsulfonamido)-2-(4-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide (2.5 g, 5 mmol, 1 eq) was dissolved in dichloromethane and cooled to −78° C. Tetrabutylammonium iodide (0.19 g, 0.5 mmol, 0.1 eq) was added to the above mixture followed by slow dropwise addition of BCl3 (25 ml) at −78° C. The above solution was stirred at room temperature for 14 h. The solution was quenched with 10% sodium bicarbonate solution and the product was extracted with dichloromethane. The dichloromethane solution was evaporated to get off-brown solid. Yield: 1.6 g (79%). 1HNMR (400 MHz, DMSO-d6): δ 1.08 (t, J=7.14 Hz, 3H), 2.71 (d, J=4.52 Hz, 3H), 3.11 (s, 3H), 3.62 (q, J=6.92 Hz, 2H), 7.14 (s, 1H), 7.30 (t, J=8.86 Hz, 2H), 7.57 (d, J=4.56 Hz, 1H), 7.81-7.82 (m, 2H), 8.72 (s, 1H), 11.32 (br s, 1H). LCMS: (ES+) m/z=407.0 (M+H).

Workup

customThe solution was quenched with 10% sodium bicarbonate solution
extractionthe product was extracted with dichloromethane
customThe dichloromethane solution was evaporated
customto get off-brown solid

Sources & evidence

ORD record: ord-bf44313e25dd4758a80ffc094117f9cd
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536338B2

Reaction notes

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