3-Pyridinemethanol → HCID 86698781, compound

HRID 338449Notes

Reaction equation

HRID 338449 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54]O)[CH:49]=1>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][N:8]2[C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:54][C:50]2[CH:49]=[N:48][CH:53]=[CH:52][CH:51]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 86698779HCID 86698779, compound

Product 1

HCID 86698781HCID 86698781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-tert-butyl 3-methyl 6-chloro-5-(4-hydroxyphenyl)-1H-indole-1,3-dicarboxylate (30 mg, 0.075 mmol), polymer supported triphenylphosphine (50 mg, 0.15 mmol), anhydrous tetrahydrofuran (1.0 mL), pyridin-3-ylmethanol (0.015 mL, 0.15 mmol), and bis(2-methoxyethyl)-diazene-1,2-dicarboxylate) (35 mg, 0.15 mmol) was sealed in a vial and stirred vigorously at 70° C. for 18 hours. The cooled reaction mixture was filtered through a pad of Celite, and the filter pad was washed with diethyl ether twice. The filtrate was concentrated in vacuo, and the residue partitioned between diethyl ether and water. The organic layer was separated and washed sequentially with water and then brine. The ether layer was concentrated in vacuo and to give the title compound, which was used directly in the next step. MS (ES+) 493 (M+1)+.

Workup

  1. customwas sealed in a vial and
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a pad of Celite
  4. washthe filter pad was washed with diethyl ether twice
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue partitioned between diethyl ether and water
  7. customThe organic layer was separated
  8. washwashed sequentially with water
  9. concentrationThe ether layer was concentrated in vacuo

Sources & evidence

ORD record
ord-593f8f1cb4de4590ac5adf50c3d500b5
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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