Trifluoroacetic acid → HCID 178434233, compound

HRID 2360447Notes

Reaction equation

HRID 2360447 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(OC(C)(C)C)=O)[N:13]=[C:12]3[CH3:25])=[CH:4][C:3]=1[F:26].BrC1C=C(F)C(N)=C(F)C=1.CC1C2C(=CC=C(B3OC(C)(C)C(C)(C)O3)C=2)N(C(OC(C)(C)C)=O)N=1.FC(F)(F)C(O)=O>ClCCl>[F:8][C:7]1[CH:6]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[CH3:25])[CH:4]=[C:3]([F:26])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6101914-Bromo-2,6-difluoroanilineHCID 57415707tert-Butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylateHCID 66997419HCID 66997419, compound2×

Product 1

HCID 178434233HCID 178434233, compoundYield 317.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure-1, tert-butyl 5-(4-amino-3,5-difluorophenyl)-3-methyl-1H-indazole-1-carboxylate (106 mg) was prepared from 4-bromo-2,6-difluoroaniline (250 mg, 1.2 mmol) and teRT-butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (559 mg, 1.56 mmol) as a white solid. teRT-butyl 5-(4-amino-3,5-difluorophenyl)-3-methyl-1H-indazole-1-carboxylate (205 mg) was dissolved in dichloromethane (4 ml), trifluoroacetic acid (0.8 ml) was added and stirred at RT for 4 h. The solvent was removed and the residue co-evaporated 4 times with dichloromethane. Solid obtained was dried under high vacuum to obtain the title compound (243 mg) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.01 (bs, 1H), 7.92 (s, 1H), 7.58 (dd, J 1.4, 8.7, 1H), 7.44 (d, J 8.7, 1H), 7.32 (dd, J 2, 8.2, 2H), 5.22 (s, 2H), 2.50 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customSolid obtained
  3. customwas dried under high vacuum

Sources & evidence

ORD record
ord-0efb3c3da35f4e43af2286ccd996fde3
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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