HCID 69015491, compound → HCID 69016749, compound

HRID 1455049Notes

Reaction equation

HRID 1455049 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC4C=CC=CC=4)[CH:22]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 69015491HCID 69015491, compound

Product 1

HCID 69016749HCID 69016749, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.15 g of 5-nitro-2-[2-(3-benzyloxyphenyl)chroman-6-yloxy]pyridine was dissolved to 600 ml of ethanol and 430 mg g of 10% palladium on charcoal was added under inert atmosphere. Starting material was hydrogenated at room temperature to give quantitative yield of 3-[6-(5-aminopyridin-2-yloxy)chroman-2-yl]phenol 1H NMR (400 MHz, d6-DMSO) δ: 9.50 (bs, 1H), 7.52 (d, 1H, J 3.0 Hz), 7.17 (t, 1H, J 8.1 Hz), 7.05 (dd, 1H, J 3.0, 8.6 Hz), 6.84-6.68 (m, 7H), 5.01-4.99 (m, 3H), 2.91-2.86 (m, 1H), 2.70-2.63 (m, 1H), 2.14-2.08 (m, 1H), 1.96-1.89 (m, 1H).

Workup

  1. additionwas added under inert atmosphere
  2. customwas hydrogenated at room temperature

Sources & evidence

ORD record
ord-6257737171d34814b4a48fdb663d5386
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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