N2,N2-Dimethyl-2,3-pyridinediamine → 3-(2-dimethylamino-pyridin-3-ylamino)-5-(1H-indol-4-yl)-phenol

HRID 1784880Notes

Reaction equation

HRID 1784880 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH:20]=[CH:21][N:22]3[Si](C(C)C)(C(C)C)C(C)C)[CH:5]=[C:6]([O:8]CC2C=CC(OC)=CC=2)[CH:7]=1.[CH3:37][N:38]([CH3:46])[C:39]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][N:40]=1>>[CH3:37][N:38]([CH3:46])[C:39]1[C:44]([NH:45][C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)[CH:3]=2)=[CH:43][CH:42]=[CH:41][N:40]=1

Participants

3

Reactant 2

HCID 15656134N2,N2-Dimethyl-2,3-pyridinediamineHCID 50993867HCID 50993867, compound

Product 1

HCID 156032813-(2-dimethylamino-pyridin-3-ylamino)-5-(1H-indol-4-yl)-phenol

Procedure

Dimethyl-(3-nitro-pyridin-2-yl)-amine was obtained as a byproduct from the reaction of 2-chloro-3-nitro-pyridine with pent-4-en-1-ol (2 eq.) and sodium hydride (3 eq.) in DMF at 100° C. overnight. To this compound (0.122 g) in a mixture of ethyl acetate/methanol (5 mL, 1:1) was added 10% Pd on carbon (24 mg). The reaction mixture was hydrogenated at 50 psi hydrogen overnight. After filtration and removal of the solvents, dimethyl-(3-amino-pyridin-2-yl)-amine (0.100 g, 100%) was obtained. 4-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole and dimethyl-(3-amino-pyridin-2-yl)-amine were coupled as described for Example 82. Deprotection as described in Example 35 gave 3-(2-dimethylamino-pyridin-3-ylamino)-5-(1H-indol-4-yl)-phenol. 1H NMR (400 MHz, CD3OD): δ 7.74 (dd, J=4.8, 1.5 Hz, 1H), 7.57 (dd, J=7.9, 1.4 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.22 (d, J=3.3 Hz, 1H), 7.11 (t, J=7.7 Hz, 1H), 7.05 (dd, J=7.3, 0.8 Hz, 1H), 6.86-6.81 (m, 2H), 6.72 (t, J=1.7 Hz, 1H), 6.62 (d, J=3.1 Hz, 1H), 6.52-6.48 (m, 1H), 2.80 (s, 6H).

Sources & evidence

ORD record
ord-4a0d31e72cd5419d88557d9ca46e59c5
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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