Sodium → HCID 59422522, compound

HRID 500020Notes

Reaction equation

HRID 500020 reaction equation
COC1C=CC=C2C=1C=CN2C1C=CC(N)=CC=1.[I:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:34]3[C:29](=[C:30]([O:35][CH3:36])[CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27]2)=[CH:22][CH:21]=1.[Na]>>[I:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:34]3[C:29](=[C:30]([O:35][CH3:36])[CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 5360545SodiumHCID 59422533HCID 59422533, compoundHCID 59422541HCID 59422541, compound

Product 1

HCID 59422522HCID 59422522, compound

Procedure

The synthesis of 1-(4-iodophenyl)indolin-4-ol (92) is provided in Reaction Scheme 4b. The reaction of 1-fluoro-4-nitrobenzene and 4-methoxy-1H-indole in the presence of Cs2CO3 gave 4-methoxy-1-(4-nitrophenyl)-1H-indole (88), which was reduced with H2/Pd to yield 4-(4-methoxy-1H-indol-1-yl)benzenamine (89). The amino group of 89 was converted via the Sandmeyer reaction to 1-(4-iodophenyl)-4-methoxy-1H-indole (90) which on reduction with sodium borocyanohyride gave 1-(4-iodophenyl)-4-methoxyindoline (91). The indoline 91 was demethylated with BBr3 to provide the desired 92.

Sources & evidence

ORD record
ord-83e4e00311034d089aefae861cb6ac58
Source dataset
uspto-grants-2010_08
Patent number
US07767834B2

Reaction notes

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