Benzylamine → HCID 67021195, compound

HRID 735473Notes

Reaction equation

HRID 735473 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=4[F:39])[N:20]=[C:21]4[C:26]=3[CH:25]=[CH:24][CH:23]=[C:22]4[C:27]([F:30])([F:29])[F:28])[CH:13]=2)[CH:5]=1.COC(=O)C1C=CC(COC2C=CC(C3N(CC4C=CC=CC=4)N=C4C=3C=CC=C4C(F)(F)F)=CC=2)=CC=1.[CH2:79]([NH2:86])[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1.C([Mg]Br)CCC>C1COCC1.CCOCC>[CH2:79]([NH:86][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=4[F:39])[N:20]=[C:21]4[C:26]=3[CH:25]=[CH:24][CH:23]=[C:22]4[C:27]([F:28])([F:30])[F:29])[CH:13]=2)[CH:5]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 67021031HCID 67021031, compoundHCID 67021354HCID 67021354, compoundHCID 178418682HCID 178418682, compound

Product 1

HCID 67021195HCID 67021195, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Fifty-seven milligrams (57 mg; 0.1 mmol) of 3-[3-(2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl)-phenoxymethyl]-benzoic acid methyl ester (prepared similarly to that of 4-[4-(2-benzyl-7-trifluoromethyl-2H-indazol-3-yl)-phenoxymethyl]-benzoic acid methyl ester in preparation of Example 2) were dissolved in 2 ml of dry THF followed by the addition of 110 μl of benzylamine (1 mmol). The reaction mixture was cooled to −30° C. and 450 μl of 2M solution of butylmagnesiumbromide in ether were added dropwise. Then the reaction mixture was stirred for 30 min at −30° C. and left overnight at 0° C. The reaction mixture was quenched with aq NH4Cl solution and product was extracted with EtOAc. Flash column chromatography (SiO2, dichloromethane as an eluant) afforded N-benzyl-3-({3-[2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}methyl)benzamide in 66% yleld.

Workup

  1. customin preparation of Example 2)
  2. waitleft overnight at 0° C
  3. customThe reaction mixture was quenched with aq NH4Cl solution and product
  4. extractionwas extracted with EtOAc

Sources & evidence

ORD record
ord-b3806ffd9a9848f7b7e629c0cdb8ebc2
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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