2-Methoxyethanol → HCID 66806706, compound

HRID 1057186Notes

Reaction equation

HRID 1057186 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:38][CH3:39])=[C:9](\[C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=2)/[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:14]=[CH:13]3)=[CH:4][CH:3]=1.[CH3:40][O:41][CH2:42][CH2:43]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:40][O:41][CH2:42][CH2:43][O:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[CH2:38][CH3:39])=[C:9](\[C:25]2[CH:26]=[CH:27][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][CH:30]=2)/[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[N:14]=[CH:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 69281165HCID 69281165, compound

Product 1

HCID 66806706HCID 66806706, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-ethyl 3-(4-((E)-2-(4-hydroxyphenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate (222 mg, 0.42 mmol), 2-methoxyethanol (0.1 mL, 1.26 mmol), diisopropyl azidocarboxylate (0.24 mL, 1.26 mmol), and triphenylphosphine (330 mg, 1.26 mmol) in THF (5 mL) was stirred at room temperature overnight. The reaction mixture was absorbed on silica gel and purified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes to afford 139 mg of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.11 (s, 1H), 7.72 (d, 1H), 7.62 (s, 1H), 7.48 (d, 1H), 7.40 (d, 2H), 7.21 (d, 1H), 7.08 (d, 2H), 6.88 (d, 2H), 6.79 (d, 2H), 6.47 (d, 1H), 5.85 (dd, 1H), 4.13 (qt, 2H), 4.02 (m, 2H), 3.90 (m, 1H), 3.74 (m, 1H), 3.62 (m, 2H), 3.29 (s, 3H), 2.47-2.37 (m, 3H), 2.01 (m, 2H), 1.76 (m, 1H), 1.59 (m, 2H), 1.22 (t, 3H), 0.89 (t, 3H).

Workup

  1. customThe reaction mixture was absorbed on silica gel
  2. custompurified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e603eb483d66477a96eb1a5bd3fdcb40
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

Loading…