Ethyl Acetate → HCID 58529284, compound

HRID 1972966Notes

Reaction equation

HRID 1972966 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:15]=[CH:16][C:17]4[C:21]([CH:22]=3)=[N:20][N:19]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=4)[CH:9]=[C:10]([CH2:11][CH2:12]O)[N:6]2[N:5]=[CH:4][N:3]=1.C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>C1COCC1>[CH2:23]([N:19]1[CH:18]=[C:17]2[C:21]([CH:22]=[C:14]([C:8]3[CH:9]=[C:10]([CH2:11][CH2:12][Br:31])[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:15]=[CH:16]2)=[N:20]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58529599HCID 58529599, compound

Product 1

HCID 58529284HCID 58529284, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-ethanol (210 mg, 0.55 mmol) in anhydrous THF (5.5 mL) at 0° C. was added carbon tetrabromide (235.5 mg, 0.71 mmol, 1.3 eq) and triphenylphosphine (157.6 mg, 0.60 mmol, 1.1 eq), and the reaction mixture was stirred at rt for 16 h. The reaction was poured into EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by MPLC (Biotage®) eluted with 15% acetone/DCM to give 222.6 mg (91%) of desired product as a white solid. 1H-NMR (300 MHz, DMSO-d6) 8.55 (s, 1H), 7.93 (s, 1H), 7.81 (d, 1H), 7.58 (s, 1H), 7.36 to 7.15 (m, 5H), 7.13 (d, 1H), 6.73 (s, 1H), 5.65 (s, 2H), 3.82 (t, 2H), 3.46 (t, 2H); ES-MS m/z 447.3/449.2 [M+H]+, RT (min) 2.91.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by MPLC (Biotage®)
  6. washeluted with 15% acetone/DCM

Sources & evidence

ORD record
ord-3790ab6fcfca48a0a4164dbb945380d5
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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