Sodium hydride → HCID 45103348, compound

HRID 908428Notes

Reaction equation

HRID 908428 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:13][OH:14].F[C:16]1[C:21]2[N:22]=[C:23]([C:25]3[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=3)[O:24][C:20]=2[CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH2:13][O:14][C:16]1[C:21]2[N:22]=[C:23]([C:25]3[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=3)[O:24][C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 817502,4-Dimethoxybenzyl alcoholHCID 45103347HCID 45103347, compound

Product 1

HCID 45103348HCID 45103348, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.08 g, 60% in mineral oil) was added to a stirred solution of (2,4-dimethoxyphenyl)methanol (4.54 g) dissolved in tetrahydrofuran (150 ml) over a period of 5 minutes at 0° C. After 30 minutes, 3-(4-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (1.547 g) was added and the mixture was heated to reflux for 16 hours. The THF was evaporated, water was added and the resultant solid was filtered and washed with water. The solid was then triturated with diethyl ether and dried with phosphorus pentoxide under reduced pressure to afford 3-[4-[(2,4-dimethoxyphenyl)methoxy]-1,3-benzoxazol-2-yl]pyridin-2-amine (2.32 g) as a solid. NMR Spectrum: (CDCl3) 3.82 (s, 3H), 3.86 (s, 3H), 5.41 (s, 2H), 6.50 (dd, 1H), 6.51 (s, 1H), 6.75 (dd, 1H), 6.91 (d, 1H), 6.96 (bs, 2H), 7.17 (d, 1H), 7.24 (d, 1H), 7.41 (d, 1H), 8.20 (dd, 1H), 8.29 (dd, 1H); Mass spectrum: M+H+ 378

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe THF was evaporated
  4. additionwater was added
  5. filtrationthe resultant solid was filtered
  6. washwashed with water
  7. customThe solid was then triturated with diethyl ether
  8. dry with materialdried with phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-75520c9d85344797836fca1b272e54c6
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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