1-Phenyl-2-propanol → 3-Bromo-7-(1-methyl-2-phenylethoxy)furo[3,2-c]pyridin-6-ylamine

HRID 912048Notes

Reaction equation

HRID 912048 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([N+:12]([O-])=O)=[C:10]([OH:11])[C:5]=2[O:4][CH:3]=1.[C:15]1([CH2:21][CH:22](O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ClC1C(F)=CC=C(Cl)C=1[C@H](OC1C2OC=CC=2C=NC=1[N+]([O-])=O)C>[Fe].Cl>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:12])=[C:10]([O:11][CH:22]([CH3:23])[CH2:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:5]=2[O:4][CH:3]=1

Participants

5

Reactant 3

HCID 941851-Phenyl-2-propanolHCID 578123753-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol2×HCID 578124747-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine

Product 1

HCID 578123843-Bromo-7-(1-methyl-2-phenylethoxy)furo[3,2-c]pyridin-6-ylamine

Reagents, catalysts & solvents 1

HCID 86633186Hydrochloric acid-ironCatalyst

Procedure

3-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol (Intermediate 10) was reacted with racemic 1-phenylpropan-2-ol following the procedure described for Intermediate 8. The resulting intermediate was reacted with iron/HCl as described in Example 2 to give the title compound. MS (ES+): m/z 347.22/349.23 (100/99) [MH+]. HPLC: tR=0.81 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, CD3OD): δ=1.32 (d, J=6.1 Hz, 3H), 2.93 (dd, J=13.5, 6.2 Hz, 1H), 3.10 (dd, J=13.6, 6.6 Hz, 1H), 4.98 (m, 1H), 7.13-7.21 (m, 1H), 7.25 (d, J=4.3 Hz, 4H), 7.70 (s, 1H), 7.82 (s, 1H).

Sources & evidence

ORD record
ord-59ae59ca20d5403f8108a12f9b45921c
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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