Triethylsilane → HCID 68795558, compound

HRID 1632024Notes

Reaction equation

HRID 1632024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:28]=[N:27][N:26]=[N:25]4)=[CH:20][CH:19]=3)=O)[C:9]=2[F:29])[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.[OH-].[NH4+]>C(O)(C(F)(F)F)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:28]=[N:27][N:26]=[N:25]4)=[CH:20][CH:19]=3)[C:9]=2[F:29])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 14923Ammonium HydroxideHCID 69000277HCID 69000277, compound

Product 1

HCID 68795558HCID 68795558, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To (3′-chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-(4-tetrazol-1-yl-phenyl)-methanone synthesized above (0.1 g, 0.24 mmol) in TFA (1.5 mL) was added triethylsilane (0.28 g, 2.4 mmol). The reaction mixture was stirred at room temperature for 20 h. The reaction mixture was cooled to 0° C., diluted with water (3 mL), basified with ammonium hydroxide solution (28%), filtered, washed with water dried to afford 0.08 g (81%) of 1-[4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenyl]-1H-tetrazole (P-404) as off-white solid. 1H NMR (DMSO-d6, 400 MHz): 7.2-7.4 (m, 6H), 7.04-7.12 (s, 3 H), 6.7 (d, J=8.4 Hz, 1H), 3.95 (s, 2H), 3.77 (s, 3H) ppm; MS (APCI+): 365.1 (M−28), LC-MS: 95.9%.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3aa1d94e195d45ea85200d6ba319a4df
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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