Acetic Acid → HCID 5329350, compound

HRID 1245479Notes

Reaction equation

[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=4)=[CH:15][C:10]3=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])=[O:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:22][CH:23]=4)=[CH:15][C:10]3=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][S:25]([N:28]1[CH2:33][CH2:32][N:31]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([C:14]3[CH:13]=[CH:12][N:11]4[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:8][N:9]=[C:10]4[CH:15]=3)=[CH:17][CH:18]=2)[CH2:30][CH2:29]1)(=[O:27])=[O:26]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 4-(3-phenylimidazo[1,2-a]pyridin-7-yl)benzaldehyde (2-5, 75 mg, 0.25 mmol, 1 equiv), 4-(methylsulfonyl)piperazine (49 mg, 0.30 mmol, 1.2 equiv), sodium triacetoxyborohydride (64 mg, 0.30 mmol, 1.2 equiv), acetic acid (14 μL, 0.25 mmol, 1.0 equiv), and 4-angstrom molecular sieves (50 mg) in 1,2-dichloroethane (5 mL) was stirred at 23° C. for 18h. The reaction mixture was filtered, and the filtrate concentrated. The residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA) to provide [4-(3-phenylimidazo[1,2-a]pyridin-7-yl)phenyl]methanol (2-6) and 7-(4-{[4-(methylsulfonyl)piperazin-1-yl]methyl}phenyl)-3-phenylimidazo[1,2-a]pyridine (2-7).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated
customThe residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA)

Sources & evidence

ORD record: ord-6440d61aa30343ef9b63a351b0ff9b4b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125888B2

Reaction notes

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