Heptane → HCID 72702894, compound

HRID 1055010Notes

Reaction equation

C[Zn]C.[CH3:4]CCCCCC.Br[C:12]1[CH:13]=[C:14]([C:35]([F:38])([F:37])[F:36])[C:15]2[N:16]([N:19]=[C:20]([CH2:22][CH2:23][C:24]3[N:25]([CH3:34])[N:26]=[C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[N:28]=3)[N:21]=2)[C:17]=1[CH3:18]>O1CCOCC1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ni](Cl)Cl>[CH3:18][C:17]1[N:16]2[N:19]=[C:20]([CH2:22][CH2:23][C:24]3[N:25]([CH3:34])[N:26]=[C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[N:28]=3)[N:21]=[C:15]2[C:14]([C:35]([F:38])([F:36])[F:37])=[CH:13][C:12]=1[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

1 M dimethylzinc in heptane (70 μL, 70 μmol, Eq: 1.00) was added to 6-bromo-5-methyl-2-[2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-ethyl]-8-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridine (30 mg, 65.5 μmol, Eq: 1.00) and 1,3-bis(diphenylphosphino)propane-nickel(II) chloride (13 mg, 24.0 μmol, Eq: 0.366) in dioxane (1 ml). The mixture was heated to 100° C. for 1 h in a microwave oven. Purification by preparative HPLC gave the desired product (16 mg, 61.7%) as a white solid. MS: m/z=394.4 (M+H+)

Workup

customPurification by preparative HPLC

Sources & evidence

ORD record: ord-70266498bbd0409caf2936d8abc009a3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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