Sodium Carbonate → 1-(4-{4-[7-amino-2-(1H-pyrrolo[2,3-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone

HRID 389506Notes

Reaction equation

HRID 389506 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[N:14][N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]3)[CH:16]=2)=[C:6]2[CH:10]=[C:9](Cl)[O:8][C:7]=12.C(OC([N:33]1[C:37]2=[CH:38][N:39]=[CH:40][CH:41]=[C:36]2[C:35](B(O)O)=[CH:34]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[N:14][N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]3)[CH:16]=2)=[C:6]2[CH:10]=[C:9]([C:35]3[C:36]4[C:37](=[CH:38][N:39]=[CH:40][CH:41]=4)[NH:33][CH:34]=3)[O:8][C:7]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66759397HCID 66759397, compoundHCID 667611851-Boc-pyrrolo[2,3-c]pyridine-3-ylboronic acid

Product 1

HCID 667596051-(4-{4-[7-amino-2-(1H-pyrrolo[2,3-c]pyridin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanoneYield 29%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-{4-[4-(7-amino-2-chlorofuro[2,3-c]pyridin-4-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (45 mg, 0.13 mmol), [1-(tert-butoxycarbonyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]boronic acid (65 mg, 0.26 mmol), Na2CO3 (55 mg, 0.52 mmol) and Pd(PPh3)4 (10 mg, 0.0087 mmol) in 4:1 dioxane:water (5 mL) was degassed with N2 for 1 min, and then heated to 120° C. in a microwave reactor for 30 min. The mixture was filtered and the filtrate was purified by preparative TLC (5:1 DCM:MeOH) to afford 16 mg (29%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.79 (s, 1H), 8.28-8.27 (m, 3H), 8.16 (s, 1H), 7.93 (s, 1H), 7.86 (s, 1H), 7.25 (s, 1H), 4.71-4.68 (m, 1H), 4.57-4.54 (m, 1H), 4.13-4.09 (m, 1H), 3.37 (m, 1H), 2.85 (m, 1H), 2.21 (m, 1H), 2.13 (s, 3H), 1.95 (m, 1H); MS (ESI): 442.1 [M+H]+; HPLC tR=2.08 min (ZQ3: polar—4 min).

Workup

  1. customwater (5 mL) was degassed with N2 for 1 min
  2. filtrationThe mixture was filtered
  3. customthe filtrate was purified by preparative TLC (5:1 DCM:MeOH)

Sources & evidence

ORD record
ord-04e092c18ddd48dcb45aca23c3bda2c3
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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