2-Bromo-4-methoxyphenol → Tert-butyl 6-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

HRID 1616904Notes

Reaction equation

HRID 1616904 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]2C3CCN(C(OC(C)(C)C)=O)CC3O[C:4]=2[CH:3]=1.[C:22]([N:29]1[CH2:34][CH:33]=[CH:32][CH:31]([OH:35])[CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].BrC1C=C(OC)C=CC=1O>>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:35][CH:31]3[CH2:30][N:29]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:34][CH2:33][CH:32]3[C:6]=2[CH:7]=1

Participants

4

Reactant 3

HCID 2973822-Bromo-4-methoxyphenolHCID 177501313-Hydroxy-1,2,3,6-tetrahydropyridine, N-BOC protectedHCID 67325186Tert-butyl 7-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Product 1

HCID 67379552Tert-butyl 6-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate

Procedure

Tert-butyl 6-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate was synthesized as described for tert-butyl 7-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate P01 starting from N-boc-3-hydroxy-1,2,3,6-tetrahydropyridine and 2-bromo-4-methoxyphenol. MS m/z 402 [M+H]+

Sources & evidence

ORD record
ord-c5a3c531d414443a9280e9dc34531e23
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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