7-Bromoindole → 7-Bromoindoline

HRID 1643175Notes

Reaction equation

HRID 1643175 reaction equation
N1(S(N)(=O)=O)C2C(=CC=CC=2)CC1.[Br:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH:21]=[CH:20]2.[BH3-]C#N.[Na+]>CC(O)=O>[Br:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH2:21][CH2:20]2

Participants

5

Reactant 3

HCID 27570207-BromoindoleHCID 5003444Sodium cyanoborohydrideHCID 220706231H-Indole-1-sulfonamide,2,3-dihydro-(9CI)

Product 1

HCID 116655907-Bromoindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similarly, the route shown in Scheme 2 below exemplifies synthesis of certain 7-aryl(heteroaryl)-indoline(indole)-1-sulfonamide compounds of the present invention. To synthesize indole-1-sulfonamide compound (9), 1-bromo-2-nitrobenzene (6) is reduced to afford 7-bromo-1H-indole (7), which reacts with 4-methoxyphenylsulfonyl chloride to provide 7-bromo-1-(4-methoxyphenylsulfonyl)-1H-indole (8). The sulfonamide (8), is then treated with an aryl or heteroaryl boronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (9). To synthesize indoline-1-sulfonamide compound (12), 7-bromo-1H-indole (7) is further reduced (with NaCNBH3 and CH3COOH, at room temperature) to afford 7-bromoindoline (10), which reacts with a substituted phenylsulfonyl chloride to provide bromo-indoline-sulfonamide (11). The bromo-indoline-sulfonamide (11) is then treated with an aryl or heteroaryl boronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (12), which can be further modified to obtain compound (13).

Sources & evidence

ORD record
ord-6870599bcf784627ac3b3fb7fcf01e10
Source dataset
uspto-grants-2012_02
Patent number
US08119683B2

Reaction notes

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