HCID 21865169, compound → HCID 135516888, compound

HRID 857683Notes

Reaction equation

HRID 857683 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[C:15]1[N:20]=[CH:19][N:18]=[C:17]([O:21][C:22]2[CH:31]=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[N:29]3)=[CH:24][CH:23]=2)[CH:16]=1>C(Cl)Cl>[N:29]1[C:30]2[C:25](=[CH:24][CH:23]=[C:22]([O:21][C:17]3[N:18]=[CH:19][N:20]=[C:15]([C:6]4[CH:7]=[CH:8][C:9]([C:11]([F:13])([F:12])[F:14])=[CH:10][C:5]=4[OH:4])[CH:16]=3)[CH:31]=2)[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 21865169HCID 21865169, compound

Product 1

HCID 135516888HCID 135516888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 7-[6-(2-methoxymethoxy-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline, (Example 190), (1.1 g, 2.5 mmol) in CH2Cl2 (25 mL) at −78° C. was added borontrifluoride diethyl etherate (0.95 mL, 7.6 mmol, Aldrich). The reaction mixture was allowed to warm to 0° C. over 1 h and then left to stir at room temperature for 16 h. The reaction mixture was quenched with satd NaHCO3 at 0° C. The organic phase was separated, and the aqueous phase was extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuum. The crude yellow solid was suspended in MeOH, collected by filtration, washed with MeOH, and dried under high vacuum to give the title compound as a light-yellow solid. MP: 210.5–212.3° C. MS (ESI, pos. ion) m/z: 384 (M+1), 382 (M−1). Anal. Calcd for C20H12F3N3O2: C, 62.67; H, 3.16; N, 10.96; F, 14.87. Found: C, 62.85; H, 3.18; N, 11.02; F, 14.57.

Workup

  1. waitleft
  2. customThe reaction mixture was quenched with satd NaHCO3 at 0° C
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. filtrationcollected by filtration
  10. washwashed with MeOH
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-4aa6c2778ccd4a398d7f94e2bcd922f7
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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