3-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine → Propane-1-sulfonic acid (2,4-difluoro-3-[5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]-methyl-phenyl)-amide

HRID 1754749Notes

Reaction equation

HRID 1754749 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.C(OC(=O)[N:28]([C:38]1[CH:43]=[CH:42][C:41]([CH:44]=O)=[C:40](F)[N:39]=1)CC1C=NC(OC)=CC=1)(C)(C)C.I[C:49]1C2C(=NC=CC=2)N([Si](C(C)C)(C(C)C)C(C)C)C=1.C(OC(=O)N(C[C:84]1[C:89]([F:90])=[CH:88][CH:87]=[C:86]([NH:91][S:92]([CH2:95][CH2:96][CH3:97])(=[O:94])=[O:93])[C:85]=1[F:98])C1C=CC(C=O)=CN=1)(C)(C)C>>[F:98][C:85]1[C:84]([NH:28][C:38]2[CH:43]=[CH:42][C:41]([CH2:44][C:10]3[C:4]4[C:5](=[N:6][CH:7]=[CH:2][CH:3]=4)[NH:8][CH:9]=3)=[CH:40][N:39]=2)=[C:89]([F:90])[C:88]([CH3:49])=[CH:87][C:86]=1[NH:91][S:92]([CH2:95][CH2:96][CH3:97])(=[O:93])=[O:94]

Participants

5

Reactant 4

HCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 57619209(6-Fluoro-5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester2×HCID 57619377[2,6-Difluoro-3-(propane-1-sulfonylamino)-benzyl]-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl esterHCID 580879285-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine2×

Product 1

HCID 86628950Propane-1-sulfonic acid (2,4-difluoro-3-[5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]-methyl-phenyl)-amide

Procedure

respectively, were prepared following the protocol of Scheme 178. P-0259 was prepared by replacing 3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 96 with 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine in Step 1 (MS [M+H+]+=506.1). P-0378 was prepared by replacing [2,6-difluoro-3-(propane-1-sulfonylamino)-benzyl]-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester 560 with (6-Fluoro-5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester 572 (prepared as described in Example 60, Scheme 177) in Step 1 (MS [M+H+]+=364.1). P-0379 was prepared by replacing both azaindole 96 with 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine and aldehyde 560 with aldehyde 572 in Step 1 (MS [M+H+]+=400.0).

Workup

  1. customrespectively, were prepared
  2. customP-0259 was prepared
  3. customP-0378 was prepared
  4. customP-0379 was prepared

Sources & evidence

ORD record
ord-c467a2df8f2949fb9cca9ee2ea570f46
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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