Hept-2-yne → HCID 68583313, compound

HRID 1951891Notes

Reaction equation

HRID 1951891 reaction equation
[CH3:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH3:7].B1C2CCCC1CCC2.B(O)O.Br[C:21]1[CH:54]=[CH:53][C:24]([CH2:25][C:26]2[N:27]([C:39]3[CH:40]=[C:41]([N:45]4[S:49](=[O:51])(=[O:50])[NH:48][C:47](=[O:52])[CH2:46]4)[CH:42]=[CH:43][CH:44]=3)[CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[Cl:38])[N:30]=2)=[CH:23][CH:22]=1>C1COCC1>[Cl:38][C:32]1[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:31]=1[C:29]1[N:30]=[C:26]([CH2:25][C:24]2[CH:53]=[CH:54][C:21]([C:2]([CH3:1])=[CH:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:22][CH:23]=2)[N:27]([C:39]2[CH:40]=[C:41]([N:45]3[S:49](=[O:50])(=[O:51])[NH:48][C:47](=[O:52])[CH2:46]3)[CH:42]=[CH:43][CH:44]=2)[CH:28]=1

Participants

6

Reactant 4

HCID 14245Hept-2-yneHCID 61668Boronic AcidHCID 789669-Borabicyclo(3.3.1)nonaneHCID 593055095-{3-[2-(4-Bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide

Product 1

HCID 68583313HCID 68583313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-heptyne (129 μL, 1 mmol) in 2 mL dry THF at 0° C. was added 2 mL 0.5 M 9-BBN solution in THF. The resulting solution was stirred at room temperature under nitrogen for 4 hr. Then it was condensed under vacuum and used as boronic acid derivative according to general procedure G, reacting with 5-{3-[2-(4-bromo-benzyl)-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,2,5-thiadiazolidine-3-one-1,1-dioxide (119 mg, 0.2 mmol) to give 5-(3-{4-(2,4-dichloro-phenyl)-2-[4-(1-methyl-hex-1-enyl)-benzyl]-imidazol-1-yl}-phenyl)-1,2,5-thiadiazolidine-3-one-1,1-dioxide.

Workup

  1. customcondensed under vacuum

Sources & evidence

ORD record
ord-20a32e98f6684dda9716988eaf86ec27
Source dataset
uspto-grants-2013_03
Patent number
US08404731B2

Reaction notes

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