Triphenylphosphine → HCID 57546129, compound

HRID 913822Notes

Reaction equation

HRID 913822 reaction equation
[Br:1][C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]2[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:44]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:3]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]2[CH2:15][Br:44]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 57546250HCID 57546250, compound

Product 1

HCID 57546129HCID 57546129, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol (198 mg, 0.48 mmol) and triphenylphosphine (253 mg, 0.96 mmol) were combined in tetrahydrofuran (3 mL) and cooled to 0° C. N-Bromosuccinimide (180 mg, 1.01 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% ethyl acetate/hexanes) gave 140 mg (61%) as a light brown oil. 1H-NMR (CDCl3, 300 MHz) δ 7.90 (s, 1H), 7.64 (s, 1H), 5.94 (s, 2H), 4.95 (s, 2H), 3.51-3.57 (m, 2H), 0.82-0.87 (m, 2H), 0.08 (s, 9H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (5% ethyl acetate/hexanes) gave 140 mg (61%) as a light brown oil

Sources & evidence

ORD record
ord-f2cb8e307981447d9789742aedfd9330
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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