HCID 17978468, compound → HCID 17978467, compound

HRID 31341Notes

Reaction equation

HRID 31341 reaction equation
NC1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]2[CH2:42][CH:41]([OH:43])[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:44][C:45]4[CH:50]=[CH:49][C:48]([N+:51]([O-])=O)=[CH:47][N:46]=4)[CH:39]=3)[O:34]2)[CH:30]=[CH:31][CH:32]=1>[Zn]>[NH2:51][C:48]1[CH:49]=[CH:50][C:45]([O:44][C:38]2[CH:39]=[C:40]3[C:35](=[CH:36][CH:37]=2)[O:34][CH:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([O:26][CH3:25])[CH:28]=2)[CH2:42][CH:41]3[OH:43])=[N:46][CH:47]=1

Participants

4

Reactant 2

HCID 17978468HCID 17978468, compoundHCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridine

Product 1

HCID 17978467HCID 17978467, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-(5-Aminopyridin-2-yloxy)2-(3-methoxyphenyl)chroman-4-ol was prepared as described for 5-amino-2-(2-phenylchroman-6-yloxy)pyridine in Example 26 using 138 mg 2-(3-methoxyphenyl)-6-(5-nitropyridin-2-yloxy)chroman-4-ol (Example 102) and 457 mg of Zn. 1H NMR (400 MHz, d6-DMSO) δ: 7.52 (d, 1H, J 3.0 Hz), 7.32 (t, 1H, J 15.7, 7.8 Hz), 7.06 (dd, 1H, 8.7, 3.0 Hz), 7.01-7.04 (m, 3H), 6.91 (dd, 1H, J 8.6, 2.4 Hz), 6.78-6.80 (m, 1H), 6.76 (d, 1H, J 8.7 Hz), 6.71 (d, 1H, J 8.6 Hz), 5.54 (d, 1H, J 6.5 Hz), 5.19 (d, 1H, J 10.6 Hz), 5.01 (s, 2H), 4.88-4.94 (m, 1H), 3.78 (s, 3H), 2.27-2.32 (m, 1H), 1.87-1.96 (m, 1H).

Sources & evidence

ORD record
ord-ce4ed1ecfee242bfa8bd5c2238aad6aa
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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