Sodium hydride → HCID 117889759, compound

HRID 930532Notes

Reaction equation

[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Cl[C:9]1[N:14]=[CH:13][C:12]2[N:15]=[C:16]([C:26]3[CH:27]=[C:28]([CH3:34])[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=3)[N:17]([CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH3:19])[C:11]=2[CH:10]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([CH2:4][O:5][C:9]2[N:14]=[CH:13][C:12]3[N:15]=[C:16]([C:26]4[CH:27]=[C:28]([CH3:34])[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=4)[N:17]([CH:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH3:19])[C:11]=3[CH:10]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

Cyclopropyl methanol (7.4 mg; 0.103 mmol) is dissolved in toluene (1 ml) and added to NaH 60% w/w (8.3 mg; 0.348 mmol). The mixture is stirred at 70° C. for 15 min under a nitrogen atmosphere. Then a mixture of (5-[6-Chloro-1-(1-pyridin-2-yl-ethyl)-1H-imidazo[4,5-c]pyridin-2-yl]-1,3-dimethyl-1H-pyridin-2-one II-21′ (30 mg; 0.079 mmol), BINAP (9.8 mg; 0.016 mmol), Pd2(dba)3 (7.2 mg; 0.008 mmol) is added in toluene (1 ml) and stirred for 2 hours at 100° C. The reaction mixture is evaporated and dissolved in DMF. The mixture is purified using reversed phase column chromatography (Method: prep. HPLC3). The product containing fractions are lyophilized to afford the desired compound.

Workup

stirringstirred for 2 hours at 100° C
customThe reaction mixture is evaporated
dissolutiondissolved in DMF
customThe mixture is purified
additionThe product containing fractions

Sources & evidence

ORD record: ord-5868d8cd47b748fba368fd8e586c7336
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296748B2

Reaction notes

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