4-(Chloromethyl)-1-trityl-1H-imidazole → 4-[7-Methyl-1-naphthalen-1-ylmethyl-2-oxo-3,3-bis-(1-trityl-1h-imidazol-4-ylmethyl)-2,3-dihydro-1h-indol-6-yl]-benzonitrile

HRID 1355678Notes

Reaction equation

HRID 1355678 reaction equation
[CH3:1][C:2]1[C:3]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[C:8](=[O:22])[CH2:7]2.Cl[CH2:32][C:33]1[N:34]=[CH:35][N:36]([C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=1>C1COCC1>[CH3:1][C:2]1[C:3]([C:23]2[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:30]=2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[C:8](=[O:22])[C:7]2([CH2:32][C:33]1[N:34]=[CH:35][N:36]([C:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:37]=1)[CH2:32][C:33]1[N:34]=[CH:35][N:36]([C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=1

Participants

4

Reactant 2

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 185077584-(7-Methyl-1-naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-1h-indol-6-yl)-benzonitrile

Product 1

HCID 881189894-[7-Methyl-1-naphthalen-1-ylmethyl-2-oxo-3,3-bis-(1-trityl-1h-imidazol-4-ylmethyl)-2,3-dihydro-1h-indol-6-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound of 13A (250 mg, 0.644 mmol) and 4-chloromethyl-1-trityl-1H-imidazole compound (694 mg, 1.93 mmol) were dissolved in 4 ml of anhydrous THF under an atmosphere of dry N2. To this solution was added 95% KHMDS (338 mg, 1.61 mmol) and the reaction mixture was subsequently stirred overnight. The reaction mixture was partitioned between ethyl acetate and aqueous saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give a pink solid which was chromatographed on flash silica gel eluting with a gradient of ethyl acetate to MeOH in ethyl acetate (10%) to give the title compound of 14A (348 mg, 52% yield).

Sources & evidence

ORD record
ord-9a2d95e21c92450e98390ddb5c97f240
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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