Trifluoroacetic acid → 5-(5-(4-hydroxy-3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-ol

HRID 603074Notes

Reaction equation

HRID 603074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:19]2[CH:20]=[C:21]3[C:27]([C:28]4[CH:29]=[CH:30][C:31]([OH:34])=[N:32][CH:33]=4)=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)[CH:6]=[CH:7][C:8]=1[O:9]CC1C=CC(OC)=CC=1.C1(S)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[OH:9][C:8]1[CH:7]=[CH:6][C:5]([C:19]2[CH:20]=[C:21]3[C:27]([C:28]4[CH:29]=[CH:30][C:31]([OH:34])=[N:32][CH:33]=4)=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7969ThiophenolHCID 178491279HCID 178491279, compound

Product 1

HCID 1784876275-(5-(4-hydroxy-3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-olYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-{5-[3-methoxy-4-(4-methoxy-benzyloxy)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyridin-2-ol (25 mg, 0.055 mmol) in 1.5 ml of dichloromethane was added 78 mg of PS-thiophenol resin (Argonaut Technologies, 1.41 mmol-g−1), followed by TFA (0.3 ml). The clear suspension was stirred at room temperature for 1 hour, then the resin was filtered off, washed with ethyl acetate, then methanol. The filtrate was evaporated and the residue was taken up in 2 ml of ethyl acetate and saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered off, washed with water, then ethyl acetate and dried in vacuo to afford 5-(5-(4-hydroxy-3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-ol as a light beige solid (15 mg, 80% yield). 1H NMR (DMSO-d6): δ 11.83 (broad s, 1H), 11.67 (broad s, 1H), 9.05 (s, 1H), 8.49 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.0 Hz, 1H), 7.88 (dd, J=3.0, 9.5 Hz, 1H), 7.74 (d, J=2.5 Hz, 1H), 7.71 (d. J=2.0 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 7.12 (dd. J=2.0, 8.5 Hz, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.44 (d, s 9.0 Hz, 1H), 3.86 (s, 3H); HPLC/MS m/z: 334.1 [MH]+.

Workup

  1. filtrationthe resin was filtered off
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water
  6. dry with materialethyl acetate and dried in vacuo

Sources & evidence

ORD record
ord-50f54af544e54b938cff603133b3a58e
Source dataset
uspto-grants-2011_03
Patent number
US07906648B2

Reaction notes

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