Boron trifluoride etherate → HCID 178427342, compound

HRID 2173996Notes

Reaction equation

HRID 2173996 reaction equation
[OH:1][CH:2]([C:22]1[C:30]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][C:28]([CH3:39])=[C:27]2[C:23]=1[CH:24]=[CH:25][N:26]2[S:40]([C:43]1[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=1)(=[O:42])=[O:41])[C:3]1[N:7](COCC[Si](C)(C)C)[C:6]2[CH:16]=[CH:17][C:18]([C:20]#[N:21])=[CH:19][C:5]=2[N:4]=1.OC(C1C(COC2C=CC=CC=2)=CC(C)=C2C=1C=CN2S(C1C=CC(C)=CC=1)(=O)=O)C1N(COCC[Si](C)(C)C)C2C=C(C#N)C=CC=2N=1.B(F)(F)F.O(CC)CC>C(Cl)Cl>[OH:1][CH:2]([C:22]1[C:30]([CH2:31][O:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:29][C:28]([CH3:39])=[C:27]2[C:23]=1[CH:24]=[CH:25][N:26]2[S:40]([C:43]1[CH:44]=[CH:45][C:46]([CH3:47])=[CH:48][CH:49]=1)(=[O:41])=[O:42])[C:3]1[NH:7][C:6]2[CH:16]=[CH:17][C:18]([C:20]#[N:21])=[CH:19][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 86701567HCID 86701567, compoundHCID 86701568HCID 86701568, compound

Product 1

HCID 178427342HCID 178427342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-2-(hydroxy(7-methyl-5-(phenoxymethyl)-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(hydroxy(7-methyl-5-(phenoxymethyl)-1-tosyl-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (160 mg, 0.231 mmol) in CH2Cl2 (2 mL) was added BF3—OEt2 (0.059 mL, 0.462 mmol) at 0° C., and then the mixture was stirred at room temperature for 2.5 h. The reaction was quenched by 7N NH3 in MeOH. The mixture was filtered off through SiO2. The SiO2 cake was washed with CH2Cl2/MeOH (c.a. 6/1). The combined organics were concentrated to give the title compound, without need of further purification. MS (ESI+) m/z 563.3 (M+H).

Workup

  1. customThe reaction was quenched by 7N NH3 in MeOH
  2. filtrationThe mixture was filtered off through SiO2
  3. washThe SiO2 cake was washed with CH2Cl2/MeOH (c.a. 6/1)
  4. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-505987731f784b09be3ffce7644cc4ef
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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